4.7 Article

Manganese-Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 14, Pages 9563-9586

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00858

Keywords

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Funding

  1. National Natural Science Foundation of China [21772117]
  2. Natural Science Basic Research Plan in Shaanxi Province of China [2018JM2049, 2018JM2050]
  3. Fundamental Research Funds for the Central Universities [GK202103047]
  4. Scientific and Technological Plan of Guangdong Province [2019B090905005]

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This study presents a manganese-catalyzed oxidation reaction for furans with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide under mild conditions with wide functional group compatibility.
Oxidation reactions have been extensively studied in the context of the transformations of biomass-derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m-CPBA and NBS, catalytic methods for the oxidative furan-recyclizations remain scarcely investigated. Given this, we report a means of manganese-catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

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